1-[(4R,6S,6aR)-6-(iodomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-fluoropyrimidine-2,4-dione → 5'-Deoxy-5'-iodo-5-fluorouridine

HRID 1834895Notes

Reaction equation

HRID 1834895 reaction equation
CC1(C)[O:9][CH:8]2[C@H:4]([C@@H:5]([CH2:19][I:20])[O:6][C@H:7]2[N:10]2[C:16](=[O:17])[NH:15][C:13](=[O:14])[C:12]([F:18])=[CH:11]2)[O:3]1>FC(F)(F)C(O)=O.O>[I:20][CH2:19][C@H:5]1[O:6][C@@H:7]([N:10]2[CH:11]=[C:12]([F:18])[C:13](=[O:14])[NH:15][C:16]2=[O:17])[C@H:8]([OH:9])[C@@H:4]1[OH:3]

Participants

3

Reactant 1

HCID 453585381-[(4R,6S,6aR)-6-(iodomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-fluoropyrimidine-2,4-dione

Product 1

HCID 108723875'-Deoxy-5'-iodo-5-fluorouridine

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

5'-Deoxy-5'-iodo-2',3'-O-isopropylidene-5-fluorouridine (4 g) was treated with trifluoroacetic acid/water (9:1, 30 ml) for 15 minutes at room temperature. The solution was evaporated to dryness, co-evaporated with ethanol (2 × 100 ml) and the residue was recrystallized from ethyl acetate. Yield = 1.865 g (88%).

Workup

  1. customThe solution was evaporated to dryness, co-evaporated with ethanol (2 × 100 ml)
  2. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-95936a0d928b4c28891dc06fd8a1fb24
Source dataset
uspto-grants-1978_01
Patent number
US04071680

Reaction notes

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